NP-MRD: Showing NP-Card for 6,7',11'-tris(acetyloxy)-3,3-dimethyl-10'-methylidene-2'-oxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-2-ylmethyl acetate (NP0142975)

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Record Information

Version

2.0

Created at

2022-09-01 21:38:34 UTC

Updated at

2022-09-01 21:38:35 UTC

NP-MRD ID

NP0142975

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,7',11'-tris(acetyloxy)-3,3-dimethyl-10'-methylidene-2'-oxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-2-ylmethyl acetate

Description

[2,7',11'-Tris(acetyloxy)-5,5-dimethyl-10'-methylidene-2'-oxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]Dodecane]-6-yl]methyl acetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. 6,7',11'-tris(acetyloxy)-3,3-dimethyl-10'-methylidene-2'-oxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-2-ylmethyl acetate is found in Isodon excisoides and Isodon rubescens. [2,7',11'-Tris(acetyloxy)-5,5-dimethyl-10'-methylidene-2'-oxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]Dodecane]-6-yl]methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161503452D          

 38 41  0  0  0  0            999 V2000
    3.6176    1.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 76 79  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1533004161503452D          

 38 41  0  0  0  0            999 V2000
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   -0.7867   -0.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6103   -0.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2350   -0.8381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4603   -1.6318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2603   -1.8335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4855   -2.6272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8349   -1.2416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 12 17  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 26 31  1  0  0  0  0
 17 31  1  0  0  0  0
 22 31  1  0  0  0  0
 24 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 22 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0142975

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1C(C)(C)CCC(OC(C)=O)C11COC(=O)C23CC(CC(OC(C)=O)C12)C(=C)C3OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O10/c1-14-19-10-20(36-16(3)30)23-27(11-19,24(14)38-18(5)32)25(33)35-13-28(23)21(12-34-15(2)29)26(6,7)9-8-22(28)37-17(4)31/h19-24H,1,8-13H2,2-7H3

> <INCHI_KEY>
JWCMFGSMZWWYAM-UHFFFAOYSA-N

> <FORMULA>
C28H38O10

> <MOLECULAR_WEIGHT>
534.602

> <EXACT_MASS>
534.246497424

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
54.25316124360306

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[2,7',11'-tris(acetyloxy)-5,5-dimethyl-10'-methylidene-2'-oxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecane]-6-yl]methyl acetate

> <ALOGPS_LOGP>
2.53

> <JCHEM_LOGP>
1.4465539186666667

> <ALOGPS_LOGS>
-4.68

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.330900929947271

> <JCHEM_POLAR_SURFACE_AREA>
131.50000000000003

> <JCHEM_REFRACTIVITY>
130.3755

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,7',11'-tris(acetyloxy)-5,5-dimethyl-10'-methylidene-2'-oxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecane]-6-ylmethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       6.753   2.413   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.891   3.689   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.565   5.073   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.355   3.580   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.681   2.195   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.543   0.919   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.079   1.028   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.705   2.522   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.485   1.656   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.941  -0.248   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.267  -1.633   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.731  -1.741   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.057  -3.126   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.920  -4.402   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.456  -4.293   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.246  -5.787   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.869  -0.466   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.170  -1.988   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.013  -3.022   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.546  -2.545   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.427  -3.603   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.143  -1.022   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.371   0.065   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.601   1.048   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.574   2.155   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.110   1.685   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.265   2.703   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.961   4.213   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.501   4.704   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       4.116   5.232   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.390   0.067   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.469  -0.310   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.006  -0.401   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.439  -1.565   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -0.859  -3.046   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      -2.352  -3.423   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -2.773  -4.904   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -3.425  -2.318   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   12    6   18   31                                             
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   31   34                                             
CONECT   23   22   24                                                       
CONECT   24   23   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
CONECT   31   26   17   22                                                  
CONECT   32   24   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   22   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Value	Source
[2,7',11'-Tris(acetyloxy)-5,5-dimethyl-10'-methylidene-2'-oxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0,]dodecane]-6-yl]methyl acetic acid	Generator
[2,7',11'-Tris(acetyloxy)-5,5-dimethyl-10'-methylidene-2'-oxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecane]-6-yl]methyl acetic acid	Generator

Chemical Formula

C₂₈H₃₈O₁₀

Average Mass

534.6020 Da

Monoisotopic Mass

534.24650 Da

IUPAC Name

[2,7',11'-tris(acetyloxy)-5,5-dimethyl-10'-methylidene-2'-oxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecane]-6-yl]methyl acetate

Traditional Name

2,7',11'-tris(acetyloxy)-5,5-dimethyl-10'-methylidene-2'-oxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecane]-6-ylmethyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1C(C)(C)CCC(OC(C)=O)C11COC(=O)C23CC(CC(OC(C)=O)C12)C(=C)C3OC(C)=O

InChI Identifier

InChI=1S/C28H38O10/c1-14-19-10-20(36-16(3)30)23-27(11-19,24(14)38-18(5)32)25(33)35-13-28(23)21(12-34-15(2)29)26(6,7)9-8-22(28)37-17(4)31/h19-24H,1,8-13H2,2-7H3

InChI Key

JWCMFGSMZWWYAM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Isodon excisoides	LOTUS Database	35616633
Isodon rubescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Kaurane diterpenoid
Pentacarboxylic acid or derivatives
Delta valerolactone
Delta_valerolactone
Oxane
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.53	ALOGPS
logP	1.45	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	131.5 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	130.38 m³·mol⁻¹	ChemAxon
Polarizability	54.25 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13919278

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6,7',11'-tris(acetyloxy)-3,3-dimethyl-10'-methylidene-2'-oxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-2-ylmethyl acetate (NP0142975)

MOL for NP0142975 (6,7',11'-tris(acetyloxy)-3,3-dimethyl-10'-methylidene-2'-oxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-2-ylmethyl acetate)

3D MOL for NP0142975 (6,7',11'-tris(acetyloxy)-3,3-dimethyl-10'-methylidene-2'-oxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-2-ylmethyl acetate)

3D SDF for NP0142975 (6,7',11'-tris(acetyloxy)-3,3-dimethyl-10'-methylidene-2'-oxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-2-ylmethyl acetate)

3D-SDF for NP0142975 (6,7',11'-tris(acetyloxy)-3,3-dimethyl-10'-methylidene-2'-oxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-2-ylmethyl acetate)

PDB for NP0142975 (6,7',11'-tris(acetyloxy)-3,3-dimethyl-10'-methylidene-2'-oxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-2-ylmethyl acetate)

3D PDB for NP0142975 (6,7',11'-tris(acetyloxy)-3,3-dimethyl-10'-methylidene-2'-oxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-2-ylmethyl acetate)

SMILES for NP0142975 (6,7',11'-tris(acetyloxy)-3,3-dimethyl-10'-methylidene-2'-oxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-2-ylmethyl acetate)

INCHI for NP0142975 (6,7',11'-tris(acetyloxy)-3,3-dimethyl-10'-methylidene-2'-oxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-2-ylmethyl acetate)

Structure for NP0142975 (6,7',11'-tris(acetyloxy)-3,3-dimethyl-10'-methylidene-2'-oxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-2-ylmethyl acetate)

3D Structure for NP0142975 (6,7',11'-tris(acetyloxy)-3,3-dimethyl-10'-methylidene-2'-oxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-2-ylmethyl acetate)